Syntheses of Enantiopure Aliphatic Secondary Alcohols and Acetates by Bioresolution with Lipase B from Candida antarctica

The lipase B from Candida antarctica (Novozym 435®, CALB) efficiently catalyzed the kinetic resolution of some aliphatic secondary alcohols: (±)-4-methylpentan-2-ol (1), (±)-5-methylhexan-2-ol (3), (±)-octan-2-ol (4), (±)-heptan-3-ol (5) and (±)-oct-1-en-3-ol (6). The lipase showed excellent enantio...

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Published in:Molecules
Main Authors: Ferreira, Hercules V., Rocha, Lenilson C., Severino, Richele P., Porto, André L. M.
Format: Text
Language:English
Published: MDPI 2012
Subjects:
Article
Antarc*
Antarctica
Online Access:http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268719/
http://www.ncbi.nlm.nih.gov/pubmed/22836214
https://doi.org/10.3390/molecules17088955
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spelling ftpubmed:oai:pubmedcentral.nih.gov:6268719 2023-05-15T13:40:41+02:00 Syntheses of Enantiopure Aliphatic Secondary Alcohols and Acetates by Bioresolution with Lipase B from Candida antarctica Ferreira, Hercules V. Rocha, Lenilson C. Severino, Richele P. Porto, André L. M. 2012-07-26 http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268719/ http://www.ncbi.nlm.nih.gov/pubmed/22836214 https://doi.org/10.3390/molecules17088955 en eng MDPI http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268719/ http://www.ncbi.nlm.nih.gov/pubmed/22836214 http://dx.doi.org/10.3390/molecules17088955 © 2012 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/). CC-BY Article Text 2012 ftpubmed https://doi.org/10.3390/molecules17088955 2018-12-16T01:21:19Z The lipase B from Candida antarctica (Novozym 435®, CALB) efficiently catalyzed the kinetic resolution of some aliphatic secondary alcohols: (±)-4-methylpentan-2-ol (1), (±)-5-methylhexan-2-ol (3), (±)-octan-2-ol (4), (±)-heptan-3-ol (5) and (±)-oct-1-en-3-ol (6). The lipase showed excellent enantioselectivities in the transesterifications of racemic aliphatic secondary alcohols producing the enantiopure alcohols (>99% ee) and acetates (>99% ee) with good yields. Kinetic resolution of rac-alcohols was successfully achieved with CALB lipase using simple conditions, vinyl acetate as acylating agent, and hexane as non-polar solvent. Text Antarc* Antarctica PubMed Central (PMC) Molecules 17 8 8955 8967
institution Open Polar
collection PubMed Central (PMC)
op_collection_id ftpubmed
language English
topic Article
spellingShingle Article
Ferreira, Hercules V.
Rocha, Lenilson C.
Severino, Richele P.
Porto, André L. M.
Syntheses of Enantiopure Aliphatic Secondary Alcohols and Acetates by Bioresolution with Lipase B from Candida antarctica
topic_facet Article
description The lipase B from Candida antarctica (Novozym 435®, CALB) efficiently catalyzed the kinetic resolution of some aliphatic secondary alcohols: (±)-4-methylpentan-2-ol (1), (±)-5-methylhexan-2-ol (3), (±)-octan-2-ol (4), (±)-heptan-3-ol (5) and (±)-oct-1-en-3-ol (6). The lipase showed excellent enantioselectivities in the transesterifications of racemic aliphatic secondary alcohols producing the enantiopure alcohols (>99% ee) and acetates (>99% ee) with good yields. Kinetic resolution of rac-alcohols was successfully achieved with CALB lipase using simple conditions, vinyl acetate as acylating agent, and hexane as non-polar solvent.
format Text
author Ferreira, Hercules V.
Rocha, Lenilson C.
Severino, Richele P.
Porto, André L. M.
author_facet Ferreira, Hercules V.
Rocha, Lenilson C.
Severino, Richele P.
Porto, André L. M.
author_sort Ferreira, Hercules V.
title Syntheses of Enantiopure Aliphatic Secondary Alcohols and Acetates by Bioresolution with Lipase B from Candida antarctica
title_short Syntheses of Enantiopure Aliphatic Secondary Alcohols and Acetates by Bioresolution with Lipase B from Candida antarctica
title_full Syntheses of Enantiopure Aliphatic Secondary Alcohols and Acetates by Bioresolution with Lipase B from Candida antarctica
title_fullStr Syntheses of Enantiopure Aliphatic Secondary Alcohols and Acetates by Bioresolution with Lipase B from Candida antarctica
title_full_unstemmed Syntheses of Enantiopure Aliphatic Secondary Alcohols and Acetates by Bioresolution with Lipase B from Candida antarctica
title_sort syntheses of enantiopure aliphatic secondary alcohols and acetates by bioresolution with lipase b from candida antarctica
publisher MDPI
publishDate 2012
url http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268719/
http://www.ncbi.nlm.nih.gov/pubmed/22836214
https://doi.org/10.3390/molecules17088955
genre Antarc*
Antarctica
genre_facet Antarc*
Antarctica
op_relation http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268719/
http://www.ncbi.nlm.nih.gov/pubmed/22836214
http://dx.doi.org/10.3390/molecules17088955
op_rights © 2012 by the authors; licensee MDPI, Basel, Switzerland.
http://creativecommons.org/licenses/by/3.0/
This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
op_rightsnorm CC-BY
op_doi https://doi.org/10.3390/molecules17088955
container_title Molecules
container_volume 17
container_issue 8
container_start_page 8955
op_container_end_page 8967
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